Tetrahydrofuran → HCID 53846483, compound

HRID 366424Notes

Reaction equation

[H-].[Na+].O[C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][C:9]2=[O:14].[C:15]1([CH:21]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30]Br)[CH2:24][CH2:23]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C[O:41]CC1>>[C:15]1([CH:21]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30][O:14][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[CH2:11][CH2:12][C:13](=[O:41])[CH2:4]4)[CH2:24][CH2:23]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 1199215-Hydroxy-1-tetralone

HCID 232892181-(3-Bromopropyl)-4-(diphenylmethyl)piperazine

Product 1

HCID 53846483HCID 53846483, compoundYield 83%

Conditions

Temperature: 50 °C

Procedure

A suspension of sodium hydride (11 mg 60% oil dispersion, 0.28 mmol) and 5-hydroxy-1-tetralone (43 mg, 0.27 mmol) in 5 mL of THF was warmed to about 50° C. for about 30 min. After addition of N-diphenylmethyl-N'-(3-bromopropyl)piperazine (100 mg, 0.27 mmol) the mixture was stirred at about 50° C. for about 3 h. Evaporation of the solvent and silica gel chromatography of the residue (diethyl ether-CH2Cl2 =1:4) gave 100 mg (83%) of the title compound as an oil; MS 455.4.

Workup

customEvaporation of the solvent and silica gel chromatography of the residue (diethyl ether-CH2Cl2 =1:4)

Sources & evidence

ORD record: ord-8a30f9fc5c104fa08a1624e1f33a21ad
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130217

Reaction notes

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